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Playoff berths: 4 (1986 WS, 1988, 1999, 2000 WS)
Best season: 1986 (108-54, World Series champions)
Highlights: 1986 World Series, 2000 World Series, Mike Piazza trade, 1988 and 1999 Playoff appearances, 9/21/01
Lowlights: The Worst Teams Money Could Buy (1992,1993), 1994 MLB Strike, Generation K.
Shocking, isn't it? Shocking to find that Fred Wilpon somehow got to the top of the list. Well, here's why.
With the help of Nelson Doubleday, Wilpon was part of the team's glory days, when they were one of the best teams in baseball. The pieces having already been acquired in the draft, trades, and free agency, the Mets went on to win 108 games en route to a dramatic seven game series with Boston.
Two years later, the Mets made it back into the postseason, only to fall to the upstart Dodgers.
The Mets regressed under the Doubleday/Wilpon group in the early 1990's. Back to back disappointing seasons in 1992 and 1993 gave the team the moniker "the Worst Team Money Could Buy."
Fortunately, after a strike shortened 1994 and 1995, and a rebuilding 1996 and 1997, the Mets were back in business, acquiring solid pieces that would contribute to the 1999 and 2000 NL Wild Card teams.
Payson and Doubleday/Wilpon hold the distinction of being the owners of the two World Series champions, as well as their two other NL pennants. Though the Wilpon part (regrettably) lives on, the owners of the team during two successful runs clearly is the best one in team history.